Challenges can be catalysts which lead to either positive or negative outcomes. Are you challenging yourselves as a unit to move forward, or is your “challenge of the moment” an issue holding you back? Are you prepared, willing and ready to take the next steps toward accelerating family and business growth? Is there an unseen or unaddressed issue that could destroy family harmony? Where can you go to learn what others in your circumstances may have experienced? Here are some common obstacles business families face.


Family and trust are not synonymous. What if trust has been broken? Is there a way to rebuild? Who leads this process and what methods are commonly used?

The trust-challenge is not new, but there is help. Many family members regain trust over time. However, left unaddressed, trust issues can leave deep wounds for generations. This is also one of the primary family enterprise destroyers. Whether there are feelings of isolation, being misunderstood, or feeling like a black sheep, avoiding this topic can undermine the work a family has done to build a collective future.

The rebuilding process can begin with just one person.


Finding a collective purpose can be a challenge, especially while working with different perspectives. History demonstrates that flags, crests and even the weave of a fabric have been used to represent the essence and meaning of family. If you own a company you likely have a vision or value statement connected to the enterprise. Do you have one for your family? People want to belong to something they are proud of and this especially rings true for families.

Does your family have a stated common goal, a set of values everyone rallies around or a clear shared intent? If your purpose is continued wealth creation, is there a role for the non-business oriented family members? How can everyone contribute, be included, and demonstrate their unique value in your enterprising family ecosystem?

The Experience Gap

One of the greatest challenges that enterprising families face is their transition process. (Succession or Continuity) There is often a knowledge and an experience gap between generations. When the wealth creator or current CEO is ready to transition his or her leadership role who will step forward?

The right candidate may be at the table but how do you bridge a twenty-plus year experience gap? Knowledge can be transferred but some things just come with time. Are your expectations realistic for the next generation? What is at risk if you transition too quickly or not soon enough?

Individual or Collective

Families are made up of individuals. Each person has his or her own hopes, dreams, goals and objectives. At times, being part of an enterprising family can create conflicting agendas between a person, their own household and the extended family as a group.

How can you encourage and maintain healthy individuals while holding together your family unit? What have others done to create this harmony and thrive as a collective?

Entitlement Explained

No one sets out to be perceived as entitled. However, having met many multigenerational families, there are times where “entitlement” feelings may be explainable.

“I started sweeping floors when I was nine, helped with the books by 16, never got to be in sports because we had to keep the doors open and it was always business over fun. Of course I feel some of the business is mine. How could I feel any other way?”
– fourty-five-year-old father of 4 who would like to take dividends from the family business to help support lifestyle for his family. His parents see him as expressing entitlement to something that does not belong to him.

Are there ways to avoid entitlement in your young children and adult children? What tools do families use to mitigate an entitled attitude? Could normal behaviour be interpreted incorrectly because of the family’s last name or wealth?

Non-Family Board Members

Most professionals who work with enterprising families will suggest that non-family members be added to their advisory board in a non-fiduciary capacity. Many wealth creators struggle with this idea. Typically concerns over privacy and control are the basis for resisting this concept.

What are the pros and cons of non-family members providing insight and advice? Will a family member try to “stack the deck” with their preferred connections? Are you expected to disclose your financial information to these individuals? What will it cost and why should you pay them? What is the difference between an advisory board and a fiduciary board?

The greatest challenge is finding the right people with the skills that will help your enterprising family.


Governance is often cited as the secret formula which keeps a multi-generational family together and thriving. Governance is a powerful word that many people instinctively connect to “control”. However, the Greek word “kubernan” which means “to steer” is the origin of the modern word governance.

Family governance is about communication and decision making processes. With an agreed upon structure, control is not lost by anyone, but the communication and consultation process improves and families stay bonded. The journey to good governance won’t necessarily be easy, yet a family’s legacy may depend on their openness to trying.

Governance in the context of enterprising families is often misunderstood.


Giving is very personal even when it is done publicly. Agreement on philanthropy does not always come naturally. Individuals may have conflicting thoughts on philanthropy, or find it difficult to agree on where to give.

Some families are introduced to philanthropy through a proposed tax strategy while others have been discretely giving for years. Whether you are donating to a community event or gifting assets to your children, how do you create the teachable moments with your rising generations? What are the intended and unintended impacts of your generosity?

Explore methods to make a difference while integrating your values, your wealth strategy and family.

Involving your children and grandchildren in charities, volunteer work or philanthropic causes can have a meaningful impact on everyone.